Hydrochloric Acid → (2S)-2-hydroxy-3,3-dimethyl-4-[(methylsulfonyl)oxy]butyl methanesulfonate

HRID 750392노트

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HRID 750392 반응식
[CH3:1][C:2]([CH3:9])([CH2:7][OH:8])[C@H:3]([OH:6])[CH2:4][OH:5].[CH3:10][S:11](Cl)(=[O:13])=[O:12].Cl>N1C=CC=CC=1.ClCCl>[CH3:10][S:11]([O:5][CH2:4][C@@H:3]([OH:6])[C:2]([CH3:9])([CH3:1])[CH2:7][O:8][S:11]([CH3:10])(=[O:13])=[O:12])(=[O:13])=[O:12]

참가 물질

6

반응물 3

HCID 313Hydrochloric Acid2회HCID 31297Methanesulfonyl chlorideHCID 11020933(S)-3,3-Dimethylbutane-1,2,4-triol

생성물 1

HCID 58981714(2S)-2-hydroxy-3,3-dimethyl-4-[(methylsulfonyl)oxy]butyl methanesulfonate수율 52.1%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

To a 0° C. solution of 25.3 g (189 mmol) of (2S)-3,3-dimethyl-1,2,4butanetriol in 170 mL of pyridine was added dropwise 29.1 mL (378 mmol) of methanesulfonyl chloride. The reaction mixture was allowed to slowly warm to room temperature, stirred for 18 h, and then diluted with dichloromethane. To the mixture was added 200 mL of 1N hydrochloric acid followed by concentrated hydrochloric acid until the pH of the aqueous phase was brought to a value of 2. The mixture was extracted with dichloromethane, and the combined extracts were washed with brine and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10% acetone in dichloromethane to afford 21.75 g (52.10%) of (2S)-2-hydroxy-3,3-dimethyl-4-[(methylsulfonyl)oxy]butyl methanesulfonate. 1H NMR (300 MHz, DMSO-d6) δ 5.48 (d, J=6 Hz, 1H), 4.30 (dd, J=2 Hz, J=10 Hz, 1H), 3.91-4.05 (m, 3H), 3.16 (d, J=4 Hz, 6H), 0.90 (d, J=13 Hz, 6H).

후처리

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe combined extracts were washed with brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 10% acetone in dichloromethane

출처 및 근거

ORD 기록
ord-e7197860bd3641209b629162d931ce30
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402606B2

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